Why Martha Stewart Can’t Get A Date, And What She’s (Maybe) Doing To Fix It

It’s no great secret that older, rich, not-even-that-attractive men have no trouble finding younger, very attractive women to date and marry them. Think Rupert Murdoch, Harvey Weinstein, and, well, hundreds and hundreds of other wrinkly old rich men. Older, super-successful women, however, have a more difficult time with love, for a set of complicated and infuriating reasons. Increasingly, those women are turning to matchmakers.

That’s according to Paula Froelich, writing for the Daily Beast about the apparent rise in high-powered women asking for matchmakers for help. After all, these women can’t pick up guys in bars, or online — they’ll end up mocked in the gossip columns. Many of them want more than a boytoy whose company can simply be bought (ahem, Jennifer Lopez and Casper Smart).

Even more frustrating, men don’t seem to flock to these women in large numbers, either. Froelich says that long-single Martha Stewart was overheard at a dinner party a couple of years ago lamenting her lack of dating mojo. “I can’t get a date,” she told her dinner companions. “You know anyone you can set me up with?”

So, for a woman like Stewart or Tinsley Mortimer — Froelich’s examples, who may or may not be matchmaker clients — that leaves a small pool of men who are available, wealthy, serious, and age-appropriate. Plus, matchmakers say the very qualities that made these women so successful make it tricky for them to find love.

“It’s very challenging for high-powered women to get a date,” one matchmaker who specializes in Silicon Valley millionaires tells Froelich. “They’ve had to adopt certain characteristics to get ahead—aggression, being tough, ball busting—and in the dating world they will carry over more masculine characteristics, and guys don’t want that. I do a ton of date coaching to play up all strengths: never downplay your smarts or success but dealing those cards in the right fashion, accentuating your femininity. Not downplaying your achievements, but let the man be the fricking man!”

According to some of the matchmakers, successful women are rigid, manly, and “not very fun.” (Argh.) Meanwhile, men are looking for “somebody who is soft, feminine, who feels good.” (Double argh.) That is some old-school Patti Stanger-style stereotyping. Still, it’s clear that something is going on if women are outsourcing their dating needs, and paying up to $200,000 a year to do it. I’m just not sure I want to know what it is.